PKG ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259963667
Author: SMITH
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Question
Chapter 27, Problem 27.19P
Interpretation Introduction
(a)
Interpretation: The type of sigmatropic rearrangement in the given equation is to be illustrated.
Concept introduction: Sigmatropic rearrangements are pericyclic reactions which involve the migration of sigma bonds. In these reactions, old sigma bonds are broken and new sigma bonds are formed.
Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the
Interpretation Introduction
(b)
Interpretation: The type of sigmatropic rearrangement in the given equation is to be illustrated.
Concept introduction: Sigmatropic rearrangements are pericyclic reactions which involve the migration of sigma bonds. In these reactions, old sigma bonds are broken and new sigma bonds are formed.
Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
8. Draw all the resonance forms for each of the fling molecules or ions, and indicate the major
contributor in each case, or if they are equivalent (45)
(2)
-PH2
سمة
مد
A
J
то
گای ه
+0
Also calculate the amount of starting materials chlorobenzaldehyde and p-chloroacetophenone
required to prepare 400 mg of the given chalcone product 1, 3-bis(4-chlorophenyl)prop-2-en-1-one
molar mass ok 1,3-bis(4-Chlorophenyl) prop-2-en-1-one = 277.1591m01
number of moles= 0.400/277.15 = 0.00144 moles
2 x 0.00 144=0.00288 moves
arams of acetophenone = 0.00144 X 120.16 = 0.1739
0.1739x2=0.3469
grams of benzaldehyde = 0.00144X106.12=0.1539
0.1539x2 = 0.3069
Starting materials:
0.3469 Ox acetophenone,
0.3069 of benzaldehyde
3
1.
Answer the questions about the following reaction:
(a) Draw in the arrows that can be used make this reaction occur and draw in the product of substitution in this
reaction. Be sure to include any relevant stereochemistry in the product structure.
+
SK
F
Br
+
(b) In which solvent would this reaction proceed the fastest (Circle one)
Methanol
Acetone
(c) Imagine that you are working for a chemical company and it was your job to perform a similar reaction to the
one above, with the exception of the S atom in this reaction being replaced by an O atom. During the reaction, you
observe the formation of three separate molecules instead of the single molecule obtained above. What is the likeliest
other products that are formed? Draw them in the box provided.
Chapter 27 Solutions
PKG ORGANIC CHEMISTRY
Ch. 27 - Prob. 27.1PCh. 27 - Problem 27.2
For each molecular orbital in Figure...Ch. 27 - Problem 27.3
(a) Using Figure 27.2 as a guide,...Ch. 27 - Problem 27.4
(a) How many molecular orbitals are...Ch. 27 - Prob. 27.5PCh. 27 - Prob. 27.6PCh. 27 - Prob. 27.7PCh. 27 - Prob. 27.8PCh. 27 - Prob. 27.9PCh. 27 - Prob. 27.10P
Ch. 27 - Problem 27.11
What product would be formed by the...Ch. 27 - Consider cycloheptatrienone and ethylene, and draw...Ch. 27 - Problem 27.13
Show that a thermal suprafacial...Ch. 27 - Prob. 27.14PCh. 27 - a Draw the product of the following [4+2]...Ch. 27 - Prob. 27.16PCh. 27 - Prob. 27.17PCh. 27 - Problem 27.18
Using orbital symmetry, explain why...Ch. 27 - Prob. 27.19PCh. 27 - Prob. 27.20PCh. 27 - Prob. 27.21PCh. 27 - Prob. 27.22PCh. 27 - Prob. 27.23PCh. 27 - Prob. 27.24PCh. 27 - Problem 27.25
(a) What product is formed by the...Ch. 27 - Prob. 27.26PCh. 27 - Prob. 27.27PCh. 27 - Prob. 27.28PCh. 27 - Prob. 27.29PCh. 27 - Prob. 27.30PCh. 27 - Prob. 27.31PCh. 27 - Prob. 27.32PCh. 27 - Prob. 27.33PCh. 27 - Prob. 27.34PCh. 27 - Prob. 27.35PCh. 27 - Prob. 27.36PCh. 27 - Prob. 27.37PCh. 27 - Prob. 27.38PCh. 27 - Prob. 27.39PCh. 27 - Prob. 27.40PCh. 27 - 27.41 What starting materials are needed to...Ch. 27 - Prob. 27.42PCh. 27 - Prob. 27.43PCh. 27 - Prob. 27.44PCh. 27 - Prob. 27.45PCh. 27 - Prob. 27.46PCh. 27 - 27.47 What product is formed from the [5,5]...Ch. 27 - Prob. 27.48PCh. 27 - 27.49 Draw structures for A, B, and C in the...Ch. 27 - Prob. 27.50PCh. 27 - Prob. 27.51PCh. 27 - 27.52 Draw the products of each reaction.
c....Ch. 27 - Prob. 27.53PCh. 27 - 27.54 Draw a stepwise, detailed mechanism for the...Ch. 27 - Prob. 27.55PCh. 27 - Prob. 27.56PCh. 27 - Prob. 27.57PCh. 27 - 27.58 Draw a stepwise, detailed mechanism for the...Ch. 27 - Prob. 27.59PCh. 27 - Prob. 27.60PCh. 27 - Prob. 27.61PCh. 27 - Prob. 27.62PCh. 27 - Prob. 27.63P
Knowledge Booster
Similar questions
- 3. For the reactions below, draw the arrows corresponding to the transformations and draw in the boxes the reactants or products as indicated. Note: Part A should have arrows drawn going from the reactants to the middle structure and the arrows on the middle structure that would yield the final structure. For part B, you will need to draw in the reactant before being able to draw the arrows corresponding to product formation. A. B. Rearrangement ΘΗarrow_forward2. Draw the arrows required to make the following reactions occur. Please ensure your arrows point from exactly where you want to exactly where you want. If it is unclear from where arrows start or where they end, only partial credit will be given. Note: You may need to draw in lone pairs before drawing the arrows. A. B. H-Br 人 C Θ CI H Cl Θ + Br Oarrow_forward4. For the reactions below, draw the expected product. Be sure to indicate relevant stereochemistry or formal charges in the product structure. a) CI, H e b) H lux ligh Br 'Harrow_forward
- Arrange the solutions in order of increasing acidity. (Note that K (HF) = 6.8 x 10 and K (NH3) = 1.8 × 10-5) Rank solutions from least acidity to greatest acidity. To rank items as equivalent, overlap them. ▸ View Available Hint(s) Least acidity NH&F NaBr NaOH NH,Br NaCIO Reset Greatest acidityarrow_forward1. Consider the following molecular-level diagrams of a titration. O-HA molecule -Aion °° о ° (a) о (b) (c) (d) a. Which diagram best illustrates the microscopic representation for the EQUIVALENCE POINT in a titration of a weak acid (HA) with sodium. hydroxide? (e)arrow_forwardAnswers to the remaining 6 questions will be hand-drawn on paper and submitted as a single file upload below: Review of this week's reaction: H₂NCN (cyanamide) + CH3NHCH2COOH (sarcosine) + NaCl, NH4OH, H₂O ---> H₂NC(=NH)N(CH3)CH2COOH (creatine) Q7. Draw by hand the reaction of creatine synthesis listed above using line structures without showing the Cs and some of the Hs, but include the lone pairs of electrons wherever they apply. (4 pts) Q8. Considering the Zwitterion form of an amino acid, draw the Zwitterion form of Creatine. (2 pts) Q9. Explain with drawing why the C-N bond shown in creatine structure below can or cannot rotate. (3 pts) NH2(C=NH)-N(CH)CH2COOH This bond Q10. Draw two tautomers of creatine using line structures. (Note: this question is valid because problem Q9 is valid). (4 pts) Q11. Mechanism. After seeing and understanding the mechanism of creatine synthesis, students should be ready to understand the first half of one of the Grignard reactions presented in a past…arrow_forward
- Propose a synthesis pathway for the following transformations. b) c) d)arrow_forwardThe rate coefficient of the gas-phase reaction 2 NO2 + O3 → N2O5 + O2 is 2.0x104 mol–1 dm3 s–1 at 300 K. Indicate whether the order of the reaction is 0, 1, or 2.arrow_forward8. Draw all the resonance forms for each of the following molecules or ions, and indicate the major contributor in each case, or if they are equivalent. (4.5 pts) (a) PH2 سمةarrow_forward
- 3. Assign absolute configuration (Rors) to each chirality center. a. H Nitz C. он b. 0 H-C. C H 7 C. ་-4 917-417 refs H 1つ ८ ડુ d. Но f. -2- 01 Ho -OH 2HNarrow_forwardHow many signals do you expect in the H NMR spectrum for this molecule? Br Br Write the answer below. Also, in each of the drawing areas below is a copy of the molecule, with Hs shown. In each copy, one of the H atoms is colored red. Highlight in red all other H atoms that would contribute to the same signal as the H already highlighted red. Note for advanced students: In this question, any multiplet is counted as one signal. Number of signals in the 'H NMR spectrum. For the molecule in the top drawing area, highlight in red any other H atoms that will contribute to the same signal as the H atom already highlighted red. If no other H atoms will contribute, check the box at right. No additional Hs to color in top molecule For the molecule in the bottom drawing area, highlight in red any other H atoms that will contribute to the same signal as the H atom already highlighted red. If no other H atoms will contribute, check the box at right. No additional Hs to color in bottom moleculearrow_forwardIn the drawing area below, draw the major products of this organic reaction: 1. NaOH ? 2. CH3Br If there are no major products, because nothing much will happen to the reactant under these reaction conditions, check the box under the drawing area instead. No reaction. Click and drag to start drawing a structure. ☐ : A คarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY